General syntheses of 1-alkyltoxoflavin and 8-alkylfervenulin derivatives of biological significance by the regioselective alkylation of reumycin derivatives and the rates of transalkylation from 1-alkyltoxoflavins into nucleophiles

Journal of the Chemical Society. Perkin Transactions 1

Volumn , Issue 2, 2001, Pages 130-137

  Nagamatsu, Tomohisa ^a   Yamasaki, Hirofumi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; DERIVATIVES; HEATING; REDUCTION; SOLVENTS; SYNTHESIS (CHEMICAL);

NUCLEOPHILES;

AROMATIC COMPOUNDS;

EID: 0035925011     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/b007302o     Document Type: Article

References (34)

1. A.G. van Veen and J.K. Baars, Proc. Akad. Wet. (Amsterdam), 1937, 40, 498; R.A. Machlowitz, W.P. Fisher, B.S. McKay, A.A. Tytell and J. Charney, Antibiot. Chemother., 1954, 4, 259.
2. A.G. van Veen and J.K. Baars, Proc. Akad. Wet. (Amsterdam), 1937, 40, 498; R.A. Machlowitz, W.P. Fisher, B.S. McKay, A.A. Tytell and J. Charney, Antibiot. Chemother., 1954, 4, 259.
3. C. DeBoer, A. Dietz, J.S. Evans and R.M. Michael, Antibiot. Annu., 1959-1960, 220; K. Tanabe, Y. Asahi, M. Nishikawa, T. Shima, Y. Kuwada, T. Kanzawa and K. Ogata, Takeda Kenkyusho Nempo., 1963, 22, 133 (Chem. Abstr., 1964, 60, 13242).
4. C. DeBoer, A. Dietz, J.S. Evans and R.M. Michael, Antibiot. Annu., 1959-1960, 220; K. Tanabe, Y. Asahi, M. Nishikawa, T. Shima, Y. Kuwada, T. Kanzawa and K. Ogata, Takeda Kenkyusho Nempo., 1963, 22, 133 (Chem. Abstr., 1964, 60, 13242).
5. S.E. Esipov, M.N. Kolosov and L.A. Saburova, J. Antibiot., 1973, 26, 537.
6. G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1961, 83, 3094; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, Org. Chem., 1961, 26, 5256; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1962, 84, 1724; F. Yoneda, K. Shinomura and S. Nishigaki, Tetrahedron Lett., 1971, 851; E.C. Taylor and F. Sowinsky, J. Org. Chem., 1975, 40, 2321; T. Nagamatsu, H. Yamasaki and F. Yoneda, Heterocycles, 1994, 37, 1147.
7. G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1961, 83, 3094; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, Org. Chem., 1961, 26, 5256; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1962, 84, 1724; F. Yoneda, K. Shinomura and S. Nishigaki, Tetrahedron Lett., 1971, 851; E.C. Taylor and F. Sowinsky, J. Org. Chem., 1975, 40, 2321; T. Nagamatsu, H. Yamasaki and F. Yoneda, Heterocycles, 1994, 37, 1147.
8. G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1961, 83, 3094; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, Org. Chem., 1961, 26, 5256; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1962, 84, 1724; F. Yoneda, K. Shinomura and S. Nishigaki, Tetrahedron Lett., 1971, 851; E.C. Taylor and F. Sowinsky, J. Org. Chem., 1975, 40, 2321; T. Nagamatsu, H. Yamasaki and F. Yoneda, Heterocycles, 1994, 37, 1147.
9. G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1961, 83, 3094; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, Org. Chem., 1961, 26, 5256; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1962, 84, 1724; F. Yoneda, K. Shinomura and S. Nishigaki, Tetrahedron Lett., 1971, 851; E.C. Taylor and F. Sowinsky, J. Org. Chem., 1975, 40, 2321; T. Nagamatsu, H. Yamasaki and F. Yoneda, Heterocycles, 1994, 37, 1147.
10. G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1961, 83, 3094; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, Org. Chem., 1961, 26, 5256; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1962, 84, 1724; F. Yoneda, K. Shinomura and S. Nishigaki, Tetrahedron Lett., 1971, 851; E.C. Taylor and F. Sowinsky, J. Org. Chem., 1975, 40, 2321; T. Nagamatsu, H. Yamasaki and F. Yoneda, Heterocycles, 1994, 37, 1147.
11. G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1961, 83, 3094; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, Org. Chem., 1961, 26, 5256; G.D. Daves, Jr., R.K. Robins and C.C. Cheng, J. Am. Chem. Soc., 1962, 84, 1724; F. Yoneda, K. Shinomura and S. Nishigaki, Tetrahedron Lett., 1971, 851; E.C. Taylor and F. Sowinsky, J. Org. Chem., 1975, 40, 2321; T. Nagamatsu, H. Yamasaki and F. Yoneda, Heterocycles, 1994, 37, 1147.
12. S.M. Navashin, I.N. Fomina, T.G. Terent'eva and L.A. Shtegel'man, Aktual. Vopr. Sovrem. Onkol., 1973, 273 (Chem. Abstr., 1974, 81, 94f); V.K. Akimenko, N.P. Golovchenko and T.G. Terent'eva, Antibiotiki (Moscow), 1974, 19, 1101 (Chem. Abstr., 1975, 82, 132839h); V.K. Akimenko, N.P. Golovchenko and A.G. Medentsev, Mikrobiologiya, 1974, 43, 839 (Chem. Abstr., 1975, 82, 107661m); G.G. Egorenko, L.A. Shtegel'man, V.N. Solov'ev, E.K. Berezina, V.V. Berezhinskaya, M.A. Bykova, G.V. Dolgova and A.A. Firsov, Antibiotiki (Moscow), 1976, 21, 178 (Chem. Abstr., 1976, 84, 130304x); S.M. Navashin, L.P. Ivanitskaya, T.G. Terent'eva and L.V. Egorov, Farmatsiya (Moscow), 1981, 30, 55 (Chem. Abstr., 1981, 95, 73566k); A.A. Firsov, S.V. Geodakyan, M.R. Lichinitser and V.Ya. Shutka, Antibiot. Med. Biotekhnol., 1985, 30, 604 (Chem. Abstr., 1985, 103, 189153m).
13. S.M. Navashin, I.N. Fomina, T.G. Terent'eva and L.A. Shtegel'man, Aktual. Vopr. Sovrem. Onkol., 1973, 273 (Chem. Abstr., 1974, 81, 94f); V.K. Akimenko, N.P. Golovchenko and T.G. Terent'eva, Antibiotiki (Moscow), 1974, 19, 1101 (Chem. Abstr., 1975, 82, 132839h); V.K. Akimenko, N.P. Golovchenko and A.G. Medentsev, Mikrobiologiya, 1974, 43, 839 (Chem. Abstr., 1975, 82, 107661m); G.G. Egorenko, L.A. Shtegel'man, V.N. Solov'ev, E.K. Berezina, V.V. Berezhinskaya, M.A. Bykova, G.V. Dolgova and A.A. Firsov, Antibiotiki (Moscow), 1976, 21, 178 (Chem. Abstr., 1976, 84, 130304x); S.M. Navashin, L.P. Ivanitskaya, T.G. Terent'eva and L.V. Egorov, Farmatsiya (Moscow), 1981, 30, 55 (Chem. Abstr., 1981, 95, 73566k); A.A. Firsov, S.V. Geodakyan, M.R. Lichinitser and V.Ya. Shutka, Antibiot. Med. Biotekhnol., 1985, 30, 604 (Chem. Abstr., 1985, 103, 189153m).
14. S.M. Navashin, I.N. Fomina, T.G. Terent'eva and L.A. Shtegel'man, Aktual. Vopr. Sovrem. Onkol., 1973, 273 (Chem. Abstr., 1974, 81, 94f); V.K. Akimenko, N.P. Golovchenko and T.G. Terent'eva, Antibiotiki (Moscow), 1974, 19, 1101 (Chem. Abstr., 1975, 82, 132839h); V.K. Akimenko, N.P. Golovchenko and A.G. Medentsev, Mikrobiologiya, 1974, 43, 839 (Chem. Abstr., 1975, 82, 107661m); G.G. Egorenko, L.A. Shtegel'man, V.N. Solov'ev, E.K. Berezina, V.V. Berezhinskaya, M.A. Bykova, G.V. Dolgova and A.A. Firsov, Antibiotiki (Moscow), 1976, 21, 178 (Chem. Abstr., 1976, 84, 130304x); S.M. Navashin, L.P. Ivanitskaya, T.G. Terent'eva and L.V. Egorov, Farmatsiya (Moscow), 1981, 30, 55 (Chem. Abstr., 1981, 95, 73566k); A.A. Firsov, S.V. Geodakyan, M.R. Lichinitser and V.Ya. Shutka, Antibiot. Med. Biotekhnol., 1985, 30, 604 (Chem. Abstr., 1985, 103, 189153m).
15. S.M. Navashin, I.N. Fomina, T.G. Terent'eva and L.A. Shtegel'man, Aktual. Vopr. Sovrem. Onkol., 1973, 273 (Chem. Abstr., 1974, 81, 94f); V.K. Akimenko, N.P. Golovchenko and T.G. Terent'eva, Antibiotiki (Moscow), 1974, 19, 1101 (Chem. Abstr., 1975, 82, 132839h); V.K. Akimenko, N.P. Golovchenko and A.G. Medentsev, Mikrobiologiya, 1974, 43, 839 (Chem. Abstr., 1975, 82, 107661m); G.G. Egorenko, L.A. Shtegel'man, V.N. Solov'ev, E.K. Berezina, V.V. Berezhinskaya, M.A. Bykova, G.V. Dolgova and A.A. Firsov, Antibiotiki (Moscow), 1976, 21, 178 (Chem. Abstr., 1976, 84, 130304x); S.M. Navashin, L.P. Ivanitskaya, T.G. Terent'eva and L.V. Egorov, Farmatsiya (Moscow), 1981, 30, 55 (Chem. Abstr., 1981, 95, 73566k); A.A. Firsov, S.V. Geodakyan, M.R. Lichinitser and V.Ya. Shutka, Antibiot. Med. Biotekhnol., 1985, 30, 604 (Chem. Abstr., 1985, 103, 189153m).
16. S.M. Navashin, I.N. Fomina, T.G. Terent'eva and L.A. Shtegel'man, Aktual. Vopr. Sovrem. Onkol., 1973, 273 (Chem. Abstr., 1974, 81, 94f); V.K. Akimenko, N.P. Golovchenko and T.G. Terent'eva, Antibiotiki (Moscow), 1974, 19, 1101 (Chem. Abstr., 1975, 82, 132839h); V.K. Akimenko, N.P. Golovchenko and A.G. Medentsev, Mikrobiologiya, 1974, 43, 839 (Chem. Abstr., 1975, 82, 107661m); G.G. Egorenko, L.A. Shtegel'man, V.N. Solov'ev, E.K. Berezina, V.V. Berezhinskaya, M.A. Bykova, G.V. Dolgova and A.A. Firsov, Antibiotiki (Moscow), 1976, 21, 178 (Chem. Abstr., 1976, 84, 130304x); S.M. Navashin, L.P. Ivanitskaya, T.G. Terent'eva and L.V. Egorov, Farmatsiya (Moscow), 1981, 30, 55 (Chem. Abstr., 1981, 95, 73566k); A.A. Firsov, S.V. Geodakyan, M.R. Lichinitser and V.Ya. Shutka, Antibiot. Med. Biotekhnol., 1985, 30, 604 (Chem. Abstr., 1985, 103, 189153m).
17. S.M. Navashin, I.N. Fomina, T.G. Terent'eva and L.A. Shtegel'man, Aktual. Vopr. Sovrem. Onkol., 1973, 273 (Chem. Abstr., 1974, 81, 94f); V.K. Akimenko, N.P. Golovchenko and T.G. Terent'eva, Antibiotiki (Moscow), 1974, 19, 1101 (Chem. Abstr., 1975, 82, 132839h); V.K. Akimenko, N.P. Golovchenko and A.G. Medentsev, Mikrobiologiya, 1974, 43, 839 (Chem. Abstr., 1975, 82, 107661m); G.G. Egorenko, L.A. Shtegel'man, V.N. Solov'ev, E.K. Berezina, V.V. Berezhinskaya, M.A. Bykova, G.V. Dolgova and A.A. Firsov, Antibiotiki (Moscow), 1976, 21, 178 (Chem. Abstr., 1976, 84, 130304x); S.M. Navashin, L.P. Ivanitskaya, T.G. Terent'eva and L.V. Egorov, Farmatsiya (Moscow), 1981, 30, 55 (Chem. Abstr., 1981, 95, 73566k); A.A. Firsov, S.V. Geodakyan, M.R. Lichinitser and V.Ya. Shutka, Antibiot. Med. Biotekhnol., 1985, 30, 604 (Chem. Abstr., 1985, 103, 189153m).
18. T. Nagamatsu, H. Yamasaki, T. Hirota, M. Yamato, Y. Kido, M. Shibata and F. Yoneda, Chem. Pharm. Bull., 1993, 41, 362.
19. F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 1975, 23, 2001; F. Yoneda and T. Nagamatsu, Synthesis, 1975, 177; F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 1975, 23, 1885; F. Yoneda, T. Nagamatsu and K. Shinomura, J. Chem. Soc., Perkin Trans. 1, 1976, 713; F. Yoneda, Y. Sakuma, T. Nagamatsu and S. Mizumoto, J. Chem. Soc., Perkin Trans. 1, 1976, 2398.
20. F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 1975, 23, 2001; F. Yoneda and T. Nagamatsu, Synthesis, 1975, 177; F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 1975, 23, 1885; F. Yoneda, T. Nagamatsu and K. Shinomura, J. Chem. Soc., Perkin Trans. 1, 1976, 713; F. Yoneda, Y. Sakuma, T. Nagamatsu and S. Mizumoto, J. Chem. Soc., Perkin Trans. 1, 1976, 2398.
21. F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 1975, 23, 2001; F. Yoneda and T. Nagamatsu, Synthesis, 1975, 177; F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 1975, 23, 1885; F. Yoneda, T. Nagamatsu and K. Shinomura, J. Chem. Soc., Perkin Trans. 1, 1976, 713; F. Yoneda, Y. Sakuma, T. Nagamatsu and S. Mizumoto, J. Chem. Soc., Perkin Trans. 1, 1976, 2398.
22. F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 1975, 23, 2001; F. Yoneda and T. Nagamatsu, Synthesis, 1975, 177; F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 1975, 23, 1885; F. Yoneda, T. Nagamatsu and K. Shinomura, J. Chem. Soc., Perkin Trans. 1, 1976, 713; F. Yoneda, Y. Sakuma, T. Nagamatsu and S. Mizumoto, J. Chem. Soc., Perkin Trans. 1, 1976, 2398.
23. F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 1975, 23, 2001; F. Yoneda and T. Nagamatsu, Synthesis, 1975, 177; F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 1975, 23, 1885; F. Yoneda, T. Nagamatsu and K. Shinomura, J. Chem. Soc., Perkin Trans. 1, 1976, 713; F. Yoneda, Y. Sakuma, T. Nagamatsu and S. Mizumoto, J. Chem. Soc., Perkin Trans. 1, 1976, 2398.
24. T. Nagamatsu, Y. Yamagishi and F. Yoneda, Jpn. Kokai Tokkyo Koho, JP 09 255,681/1997 (Chem. Abstr., 1997, 127, 336635w).
25. M. Ozasa, T. Amakusa and T. Nagamatsu, Jpn. Kokai Tokkyo Koho, JP 10 175,807/1998 (Chem. Abstr., 1998, 129, 64309x).
26. F. Yoneda and T. Nagamatsu, J. Am. Chem. Soc., 1973, 95, 5735; F. Yoneda, T. Nagamatsu and M. Ichiba, J. Heterocycl. Chem., 1974, 11, 83.
27. F. Yoneda and T. Nagamatsu, J. Am. Chem. Soc., 1973, 95, 5735; F. Yoneda, T. Nagamatsu and M. Ichiba, J. Heterocycl. Chem., 1974, 11, 83.
28. F. Yoneda and T. Nagamatsu, Tetrahedron Lett., 1973, 1577; F. Yoneda and T. Nagamatsu, J. Heterocycl. Chem., 1974, 11, 271; F. Yoneda and T. Nagamatsu, Bull. Chem. Soc. Jpn., 1975, 48, 2884.
29. F. Yoneda and T. Nagamatsu, Tetrahedron Lett., 1973, 1577; F. Yoneda and T. Nagamatsu, J. Heterocycl. Chem., 1974, 11, 271; F. Yoneda and T. Nagamatsu, Bull. Chem. Soc. Jpn., 1975, 48, 2884.
30. F. Yoneda and T. Nagamatsu, Tetrahedron Lett., 1973, 1577; F. Yoneda and T. Nagamatsu, J. Heterocycl. Chem., 1974, 11, 271; F. Yoneda and T. Nagamatsu, Bull. Chem. Soc. Jpn., 1975, 48, 2884.
31. T. Nagamatsu and H. Yamasaki, Heterocycles, 1997, 45, 643.
32. T. Nagamatsu, Jpn. Kokai Tokkyo Koho, JP 07 41,479/1995 (Chem. Abstr., 1995, 123, 55928x).
33. T.K. Liao, F. Baiocchi and C.C. Cheng, J. Org. Chem., 1966, 31, 900.
34. F. Yoneda, M. Kawamura, T. Nagamatsu, K. Kuretani, A. Hoshi and M. Iigo, Heterocycles, 1976, 4, 1503.